Oprah (64 page)

Speaking at a fund-raiser for a community school in Baltimore, she said, “I have lots of things like all these Manolo Blahniks. I have all that and I think it’s great. I’m not one of these people, like, ‘Well, we must renounce ourselves.’ No. I have a closet full of shoes, and it’s a good thing.” She told the well-heeled crowd she enjoyed her money without guilt or apology. “I was coming back from Africa on one of my trips. I had taken one of my wealthy friends with me. She said, ‘Don’t you just feel guilty? Don’t you feel terrible?’ I said, ‘No, I don’t. I do not know how my being destitute is going to help them.’ Then I said when we got home, ‘I’m going home to sleep on my Pratesi sheets right now and I’ll feel good about it.’ ”

She recalled for her magazine readers that on her forty-second birthday she and Gayle were in Miami, where she decided to buy herself a big Cartier watch as a present. En route, she spotted a black Bentley Azure in a dealership window. “Oh, my God,” she said. “That is the most beautiful car.” She bought the Bentley on the spot. “It’s a convertible. The top is down and guess what? It starts to rain. It’s pouring.” Oprah did not put the top up on her $365,000 car. “Because I want[ed] to ride in a convertible on my birthday.” Next stop: the Cartier boutique for the Diabolo small model watch in yellow gold with all-diamond bezel, case, dial, and bracelet for $117,000.

She told viewers after attending her first couture show in Paris, “I could have bought a home for what I bought the Chanel outfits for.” She entertained at the same apex of luxury, spending millions to host parties. “Eyes have not seen, nor ears heard,” said Vernon Winfrey as he tried to describe the sumptuous events his daughter staged for Maya Angelou’s birthday every five years. Many guests recalled Maya’s
seventieth, in April 1998, as Oprah’s most opulent. She rented the
Seabourn Pride
for a week’s cruise in the Caribbean, invited two hundred people, and gave each a suite with a balcony on the luxury ship. “She even had two thousand yellow rubber duckies dropped into the ship’s pool so we could play like children in a bathtub,” recalled one guest. Their invitations arrived four months before the Easter event asking everyone for shirt size; pant size; shoe size; champagne preference; favorite liquors, foods, cosmetics, fragrances, and body lotions—all of which were stocked in their suites, along with terry-cloth robes stitched with their names. “I think she spent four million dollars on that party,” said Vernon, shaking his head as he recalled the many stops the ship made for lavish lunches on white beaches, the silk-lined tents for dinners, and the moonlit concerts with Nancy Wilson singing under the stars. Oprah threw a similar bash for Maya when she turned seventy-five; on Angelou’s eightieth birthday, Oprah rented Donald Trump’s Mar-a-Lago Club in Palm Beach for a weekend and arranged special performances by Michael Feinstein, Natalie Cole, Jessye Norman, and Tony Bennett.

In 2005, at her Montecito mansion, Oprah hosted her most lavish event, which she billed as “A Bridge to Now—A Celebration for Remarkable Women During Remarkable Times,” with cameras filming every moment for a special on ABC titled
Oprah Winfrey’s Legends Ball.
A year and a half in the planning, the event honoring black women gave the network its biggest non-sports ratings in three years. The year before, 2004, Oprah had devoted two shows to celebrating her fiftieth birthday, the first of which was said to be a “surprise” hosted by “my best friend” (Gayle King) and “my favorite white man” (John Travolta). That show, called a “modest little Super Bowl of Love” by the
Chicago Sun-Times,
was followed by an after-party at Harpo for 500 employees and then 5 days of celebration, beginning with a dinner, hosted by Stedman at Chicago’s Metropolitan Club for 75 people, including Oprah’s father and mother.

The next day they boarded Oprah’s jet and flew to California, where she was guest of honor at a ladies luncheon for 50 at the Bel-Air Hotel, her favorite LA retreat. The guests there included Salma Hayek, Diane Sawyer, Maria Shriver, Toni Morrison, Ellen DeGeneres, and Céline Dion. The following night there was a dinner dance for 200 at
a neighbor’s estate in Montecito, and the next morning a Sunday brunch for 175 people at the San Ysidro Ranch, all of which was filmed for a second Oprah show. In addition, Oprah invited
People
to cover the dinner dance staged by her party planner, Colin Cowie, full of what he called JDMs (jaw-dropping moments): 50 violinists, 200 waiters (one per guest), a chocolate-and-raspberry pound cake gilded with twenty-three-karat gold, music by Stevie Wonder, and wall-to-wall celebrities, including the Bel-Air luncheon ladies and their husbands and partners, Tom Hanks and Rita Wilson, John Travolta and Kelly Preston, Robin and Dr. Phil McGraw, Tina Turner, and Brad Pitt and Jennifer Aniston.

For “The Legends Weekend,” Oprah selected twenty-five black women she considered to be legends:

Maya Angelou (author/poet/actor/producer/director)

Shirley Caesar (singer)

Diahann Carroll (actor/singer)

Elizabeth Catlett (sculptor)

Ruby Dee (actor/playwright)

Katherine Dunham (dancer/choreographer)

Roberta Flack (singer)

Aretha Franklin (singer)

Nikki Giovanni (poet)

Dorothy Height (activist)

Lena Horne (singer/actor)

Coretta Scott King (activist)

Gladys Knight (singer)

Patti LaBelle (singer)

Toni Morrison (author)

Rosa Parks (activist)

Leontyne Price (opera singer)

Della Reese (singer/actor)

Diana Ross (singer/actor)

Naomi Sims (model)

Tina Turner (singer)

Cicely Tyson (actor)

Alice Walker (author/poet)

Dionne Warwick (singer)

Nancy Wilson (singer)

Inexplicably missing from Oprah’s list were her onetime friend Whoopi Goldberg, the singer Eartha Kitt, acclaimed opera star Jessye Norman, respected broadcaster Gwen Ifill, and Secretary of State Dr. Condoleezza Rice. Of the twenty-five women Oprah selected as legends, seven did not attend: Katherine Dunham, Aretha Franklin, Nikki Giovanni, Lena Horne, Toni Morrison, Rosa Parks, and Alice Walker. “Just too many television cameras,” said one who did not participate. “Too much Oprah.”

The “young ’uns,” as Oprah called those following in the footsteps of the “legends,” included:

Yolanda Adams (singer)

Debbie Allen (actor/dancer)

Ashanti (singer)

Tyra Banks (model/talk show host)

Angela Bassett (actor)

Kathleen Battle (opera singer)

Halle Berry (actor)

Mary J. Blige (singer)

Naomi Campbell (model)

Mariah Carey (singer)

Pearl Cleage (poet/playwright)

Natalie Cole (singer)

Suzanne De Passe (producer/writer)

Kimberly Elise (actor)

Missy Elliot (rap artist)

Pam Grier (actor)

Iman (model)

Janet Jackson (singer)

Judith Jamison (dancer/choreographer)

Beverly Johnson (model)

Chaka Khan (singer)

Gayle King (editor,
O
magazine)

Alicia Keys (singer)

Audra McDonald (actor/singer)

Terry McMillan (author)

Darnell Martin (director/screenwriter)

Melba Moore (actor/singer)

Brandy Norwood (singer)

Michelle Obama (community affairs executive)

Suzan-Lori Parks (playwright)

Phylicia Rashad (actor)

Valerie Simpson (singer/composer)

Anna Deavere Smith (actor/playwright)

Susan L. Taylor (editorial director of
Essence
)

Alfre Woodard (actor)

Oprah began the weekend with a luncheon at her estate on Friday (May 13, 2005), during which she gave six-carat diamond teardrop earrings to “the legends” and ten-carat black-and-white diamond hoop earrings to “the young ’uns,” all presented in red alligator boxes inside of which were engraved silver cases. “I’m a girl who loves a good diamond earring, you know?” Oprah told her astounded guests.

“Are they real?” asked author Terry McMillan.

“They are black diamonds, crazy love! Of course they’re real!”

During the “Legends” weekend, even the wealthiest stars were dumbfounded, especially when they saw the trolley Oprah had installed on the grounds for guests to tour “The Promised Land,” as Oprah called her rolling estate with its various promenades, pools, ponds, rose arbors, romantic bridges, and winding trails, all bordered by five thousand white hydrangeas and two thousand white flowering trees. She called her equally luxurious home in Hawaii “Kingdom Come.” As she told reporters, “I’m very biblical, you know. I got two roads to my [Hawaii] house…Glory and Hallelujah.”

But it was her home in Montecito that left guests breathless. “The driveway is five miles long, and every stone was cut by hand,” said one. “Her bathtub is a solid piece of jade, and her bathroom overlooks the entire forty-two-acre estate and gives her an eighty-degree view
of the ocean. Her closet is three thousand square feet and she has a thousand drawers for everything—yes, one thousand—sweaters and T-shirts and one hundred hats. Each drawer has a glass front so nothing gets dusty and she can see what’s inside….Gayle has her own room in the main house with rose wallpaper, and Stedman’s study overlooks the Montecito Mountains….The views throughout are magnificent….I think it’s the most beautiful house I’ve ever seen.”

The following night (Saturday, May 14, 2005), Oprah invited 362 people to a white-tie dinner dance at the Bacara Resort and Spa in Santa Barbara. She ordered 80 cases of champagne flown in from France, 120 pounds of tuna flown in from Japan, and 20,000 white peonies flown in from Ecuador. Entertainment was provided by Michael McDonald and a twenty-six-piece orchestra. Her party planner had sent his two hundred servers to waiter boot camp for three days to properly serve Oprah’s A-list celebrity guests. As everyone sat for dinner, a drum rolled and the black-tied waiters laid down 362 plates at the same moment. It was another JDM. Oprah expected no less.

That night, after a sumptuous meal and dancing, guests returned to their hotel rooms to find on their pillows a gift-wrapped souvenir photograph of the evening in a sterling-silver frame from Asprey, the jeweler who carries royal warrants from Queen Elizabeth II and the Prince of Wales. Oprah had instructed the women to wear black or white gowns for the ball, while she appeared in flaming red, just like Norma Shearer did at a black-and-white ball she threw—so everyone would look
only
at her. The following morning (Sunday, May 15, 2005), Oprah wore a tall feathered hat to host a gospel brunch at “The Promised Land,” where Senator Barack Obama, wearing sunglasses, stood under a tree a few feet away from Oprah, who had her arm draped around Barbra Streisand, swaying to the music.

Later Oprah approached Obama, who had been sworn in as a U.S. senator four months earlier. “If someone were to announce one of these days that he was going to run for president,” she said, “don’t you think this would be a sweet place to hold a fund-raiser?”

Senator Obama grinned.

B
Y THE
twenty-first century, Oprah was omnipresent, if not omnipotent. She appeared on television five days a week, claimed 44 million viewers in the United States, and was broadcast in 145 countries, from Saudi Arabia to South Africa. She was a daily presence on satellite radio (Sirius XM) with her own twenty-four-hour channel Oprah and Friends. Her monthly magazine, with her picture on every cover, had a paid circulation of 2.4 million in the United States and was published also in South Africa. Through her investment in Oxygen she was seen on cable television with segments entitled
Oprah After the Show.
When Oxygen was sold to NBC Universal, she recouped her $20 million investment and announced plans to start her own television network in 2011, to be called OWN (Oprah Winfrey Network). She produced made-for-television movies under the banner “Oprah Winfrey Presents,” and prime-time network specials. Her website,
Oprah.com
, attracted 6.7 million visitors a month, and her Twitter following numbered more than 2 million. A Google search of her name generated more than 8 million results, and there were 529 websites devoted solely to her.

By the millennium she was known and recognized throughout the country, even by those who never watched daytime television. She entered the vocabulary as a noun, a verb, and an adjective. Even
disgruntled media critics acknowledged they had entered the Oprahsphere. “She puts the cult in pop culture,” Mark Jurkowitz sniped in
The Boston Phoenix,
prompting Oprahettes to howl about the
jerk
in “Jurkowitz.” Opraholics worshipped her, and Oprahphiles studied her, making her the subject of more than three dozen PhD dissertations listed in the Library of Congress. The object of a case study on corporate success by the Harvard Business School, she was also studied at the University of Illinois at Urbana-Champaign in a course titled History 298: Oprah Winfrey, the Tycoon: Contextualizing the Economics of Race, Gender, Class in Black Business in Post–Civil Rights America.
Newsweek
declared the new century’s touchy-feely era to be the “Age of Oprah,” and
The Wall Street Journal
defined “Oprahfication” to mean “public confession as a form of therapy.”
Jet
magazine used
Oprah
as a verb: “I didn’t want to tell her…but she Oprah’d it out of me.” Politicians everywhere began “to go Oprah,” holding town meetings to let constituents vent their feelings. Companies lucky enough to have their products featured on “Oprah’s Favorite Things” experienced an avalanche of orders known as the “Oprah Effect.” By 2001, the nation had become so Oprahfied that New York’s mayor, Rudolph Giuliani, chose Oprah along with James Earl Jones to lead the memorial service at Yankee Stadium in honor of the victims of 9/11.

With the country in her thrall, Oprah finally felt secure enough to break her “no politicians” rule and wade into their divisive waters. For years she had avoided politics because she did not want to alienate her audience. “If I support one person or another, I will piss a lot of people off,” she said. “And I have not met the politician that was worth going to the mat for. When I do, I certainly will.” By staying above the political fray, she felt she retained more affection from her viewers than her highly partisan predecessor, Phil Donahue. “Oprah would not even attend a Gridiron dinner,” said former Hearst columnist Marianne Means, a past president of The Gridiron Club, whose annual dinner in Washington, D.C., is attended by the president, the vice president, and members of Congress, the Senate, and the Supreme Court. Members of the media perform skits and songs poking fun at both political parties. “We invited her many times, but she always turned us down, saying she did not get involved with politics.”

After fifteen years on the air Oprah finally decided to enter the political arena. “She waited until she was rich enough so it wouldn’t affect her bottom line,” said her cousin Katharine Carr Esters. “And that was very smart of her….But then when it comes to money, no one is smarter than Oprah.”

Once she became a fixture on the
Forbes
“400 Richest Americans” list, Oprah became part of the nation’s political conversation by extending an invitation in 2000 to the two presidential candidates to appear on her show. “I hope to create the kind of environment and ask the questions that will allow us to break the political wall and see who each one is as a person,” she said through her publicist. The next day’s news was more about Oprah going political than it was about Vice President Al Gore and Governor George W. Bush. The headline on
Salon.com
read, “The Road to the White House Goes Through Oprah.”

Politically, she appeared to be a Democrat, having contributed $1,000 in 1992 to Chicago’s Carol Moseley Braun, a Democrat and the first African American woman to be elected to the U.S. Senate. Oprah also donated $10,000 to the Democratic Senatorial Campaign Committee in 1996, and $5,000 to the Democratic National Committee in 1997. Yet she claimed to have voted “for as many Democrats as I have Republicans.” However, federal election records do not show any Republican votes, only that she voted in four Democratic primaries between 1987 and 1994. She skipped voting in the 1996, 1998, and 2000 primaries, but did cast a ballot in the general elections for president.

She once boasted to a British writer, “I think I could have a great influence in politics, and I think I could get elected.” But, she added, “I think a politician would want to be me [instead]. If you really want to change people’s lives, have an hour platform every day to go into their homes.” To
The Times
of London she said, “Having this big voice on television is what every politician wants. They all try and get on the show and I don’t do politics on the show.”

Careful at the time not to get partisan, Oprah invited First Lady Barbara Bush to be her guest in 1989, and she later extended several invitations to First Lady Hillary Rodham Clinton, who appeared four times during her husband’s eight years in the White House. Hillary celebrated her fiftieth birthday on Oprah’s show, and Oprah asked
Hillary to present her with her Lifetime Achievement Award from the International Emmys. During that ceremony, Oprah, clutching Hillary’s hand, said, “I hope you do us the privilege of running for…president of the United States.”

Oprah had considered breaking her “no politicians” rule back in 1992 by inviting Texas billionaire H. Ross Perot, Sr., to be her guest, because, as she said at the time, “He’s become larger than politics,” but she backed off. Still skittish four years later, she turned down a request from Senator Robert Dole, the 1996 GOP presidential candidate, who was running against Bill Clinton.

“I was very torn [about Dole’s request to come on the show],” she told her viewers. “I went to my producers and said, ‘Maybe this isn’t the right decision.’ But in the end I decided to stay out of politics, maintaining my long-standing policy: I don’t do politicians.” At the time, her studio audience gave her a resounding ovation. “I’ve tried to stay out of politics for my entire tenure on the air,” she said that day. “Basically, it’s a no-win situation. Over the years, I have not found that interviewing politicians about the issues worked for my viewing audience. I try to bring issues that people understand through their hearts and their feelings so they can make decisions.”

Senator Dole laughed at Oprah’s explanation. “Riiight,” he jibed years later. “She doesn’t do politicians—if they run against Democrats.”

Oprah admitted she had been “asked to do everything” at the 1996 Democratic National Convention in Chicago, but she insisted she would not participate in any way, except for attending the parties thrown by “my friends Ethel Kennedy and John Kennedy, Jr.” Since meeting Maria Shriver in Baltimore, where they both worked for WJZ-TV, Oprah had been besotted by the Kennedys. She boosted them at every turn, contributing to Ethel Kennedy’s online charity, promoting the books of Caroline Kennedy and Maria Shriver, attending fund-raisers for Kathleen Kennedy Townsend, hosting a show titled “The Kennedy Cousins,” and inviting any and all Kennedys to appear with her throughout the years. In 2009, Victoria Kennedy gave Oprah her first interview after the death of her husband, Senator Edward Kennedy.

Although Oprah had not publicly declared herself a Democrat, her close friends—Maya Angelou, Henry Louis Gates, Jr., Quincy Jones,
Coretta Scott King, Toni Morrison, Andrew Young—were all Democrats committed to Clinton, and Oprah herself had been invited to the Clintons’ first white-tie state dinner in 1994, for Japan’s emperor, Akihito, and empress, Michiko. (She admitted later she had been tongue-tied in the presence of Japanese royalty. “I didn’t know what to say, and it was one of the few times.”) Oprah had attended her first White House state dinner in 1989, during the George Herbert Walker Bush administration, with Stedman Graham, a conservative Republican, who would not accompany her to the Clinton White House five years later. So she took Quincy Jones.

“I met her that evening,” recalled the art dealer Christopher Addison, who, with his wife, owns the Addison/Ripley Fine Art gallery in Washington, D.C. “I did not recognize her as anybody famous then because I don’t watch daytime television, but the eighty-year-old woman who was my guest that evening told me who she was….Oprah had brought a little instamatic camera with her and asked me to take her photograph. I thought it was endearing of her to want her picture taken in the White House, almost like a tourist. Very sweet.”

Oprah had charmed them downstairs at the Bush White House by visiting the kitchen staff after the state dinner, but upstairs was another matter: the social staff found her to be overbearing and unreasonable. “She was rude and demanding, impossible to deal with,” Lea Berman, a former White House social secretary, told the Colonial Dames of America. “She insisted she be allowed to bring her own security into the president’s mansion. This is so against White House policy, but Ms. Winfrey became so adamant and shrill that we finally relented and allowed her to be accompanied by her own bodyguards.”

When Oprah issued her invitations to Vice President Al Gore and Governor George W. Bush in 2000 to appear on her show, both accepted because the presidential race was close, and each man wanted to reach her large female audience. A Gallup/CNN/
USA Today
poll had Bush trailing Gore by ten percentage points before the visit with Oprah; days later the same poll showed Bush in a statistical tie. News reports called it the “Oprah Bounce.” The
Chicago Sun-Times
editorial page saluted her for getting involved in the presidential race, and she
hyped her first political foray before her season’s opening show, prompting the comedian Chris Rock to joke, “Both Gore and Bush are going to appear on Oprah, but for different reasons. Gore is trying to appeal to women voters. Bush wants to find out how in the world did this black woman get all that money.”

Oprah welcomed the vice president on September 11, 2000, and he strode onstage, greeting her with a handshake and a one-armed half-hug.

“No kiss? I was hoping for something,” she teased, referring to the exceedingly long on-camera kiss Gore had planted on his wife at the Democratic Convention. “Until today I’ve stayed away from politicians, but after fifteen years I need to try to penetrate that wall,” she told her viewers as she put Gore on notice that she was going to be more grill than gush. Despite twenty-four years in public office, he demurred, “I am a little bit more of a private person than a lot of the people in the profession.” Oprah was having none of it.

“Let’s get to that kiss,” she said. “What was that all about? What did you say to your wife? Was it scripted? Were you trying to send a message?”

“I was trying to send a message to Tipper,” Gore quipped, prompting a huge laugh from the studio audience.

“No, really,” Oprah persisted. To her credit, she interrupted whenever he lapsed into his stump speech, and tried to get something more truthful and heartfelt.

“Well…I…It was an overwhelming surge of emotion. This was a great moment in our lives. I mean, it’s not as if I got there by myself. This has been a partnership, and she is my soul mate.”

The studio audience, mostly female, erupted in wild applause for the romantic robot, usually stiff and awkward, who seemed so in love with his wife after thirty years of marriage.

For an hour Oprah huffed and puffed and tried to blow “that wall” down, but all she got was Gore’s favorite movie (
Local Hero
), Gore’s favorite music (The Beatles), and Gore’s favorite cereal (Wheaties). “The woman who has persuaded hundreds of people to reveal things about themselves that might better have been kept private couldn’t get
Gore out of his comfort zone,” wrote Mark Brown in the
Chicago Sun-Times.
“Best of all for Gore, he handled her so smoothly that Oprah never seemed to realize it.”

The following week (September 18, 2000) she welcomed Governor Bush of Texas, who arrived with coconut macaroons from Texas-based Neiman Marcus for her studio audience and greeted her with a huge kiss. The photo of Bush bussing Oprah on the cheek as she smiled gleefully made the front page of
The
New York Times.

“Thanks for the kiss,” she said, sitting down next to him.

“My pleasure.” He grinned.

“There were people on the street yesterday who told me that they were going to make their decision [about who to vote for] after today’s show,” she told him. The cocky governor nodded as the cocky host dug right in and asked if he was running to restore his father’s defeat by Bill Clinton. “To get revenge?”

“Not even in the teeniest, tiniest part,” Bush insisted, saying he felt “a calling” to be president. “I see America as a land of dreams, hopes, and opportunities….”

“I wanna go behind the wall now,” snapped Oprah. “Tell us about a time when you needed forgiveness.”

“Right now,” said Bush as the studio audience erupted with laughter.

“I’m looking for specifics,” Oprah said sternly.

“I know you are, but I’m running for president.” Even she had to laugh at that, and her studio audience clapped with delight. When she asked him his “favorite dream,” he raised his right hand as if to be sworn in as president, and the studio audience again rocked with laughter. Bush later got teary-eyed as he discussed his wife’s difficult pregnancy and the birth of their twin daughters. He admitted that he finally stopped drinking at the age of forty because alcohol had taken over his life.